The Second Time Around
by Elsie Plateau
Summary: Is it possible for a word as simple as no to hurt like a dagger going through one's heart? Nearly two years after Rory rejected him, Jess is forced to return to Stars Hollow to attend Luke and Lorelei's wedding. Will sparks reignite or will Jess have move
1. Shattered

**Disclaimer: I do not own Gilmore Girls or any of its characters.**

_So, my first Gilmore Girl fanfic. Don't really know where this story is going yet, but I guess you guys will just have to read to find out, won't you? Enjoy! And please, don't hesitate to review. Thanks a million! _

**Chapter I: Shattered**

Uncertainty. Jess Mariano was a man of unpredictable measures, unrestrained by the ethical norms of society. He lived life with a sense of adventure, without a care about anyone else but himself. That is, until he met _her_. Rory Gilmore, a simple, small town girl, with an untainted reputation. She was beautiful, kind, and above all remarkably smart. They were of two different worlds: she was pampered with love and joy from a caring circle of family and friends, while he wandered amidst a solitary sea of pain and neglect. And yet, there was a certain charm about this girl that attracted him. Maybe it was their shared passion for books. Jess was an avid reader, and to find someone who had journeyed through the endless pages of classic volumes as he did enticed him.

And yet, perhaps it was her faith in him. Of anyone is Stars Hollow Rory was the only one who saw the good in him. She trusted in his abilities and intelligence, knowing that he had the potential to be a better person. But he let her down. He lied to her, deceived her, and abandoned her. He had to live with the burden of her disappointment, forever the prisoner of his own guilt. There was no escape.

_No._ That word continually echoed in his mind. How one simple word could shatter a glass of hopes and dreams. But he shouldn't have expected anything less. Did he really believe she would go away with him? No, of course not. She was too smart for that. Unlike him, she had a life, a future. He had nothing.

"Jess?" called a faint voice. "Jess, are you there?"

Jess groaned lazily, as he tossed the blanket over his head. He was in no mood to get up. It seemed like all of the problems in his life finally took their toll on him.

At the sound of continual knocking at the door Jess sat up and exclaimed, "Go away! I don't want to talk."

The young man stood up and stretched. Scratching his dark disheveled hair, he glanced around his rundown apartment. What a mess. Articles of clothing were scattered everywhere, along with magazines and beer bottles. In one corner of the residence, empty pizza boxes were stacked alongside the wall, near a twenty-year-old TV. Dirty dishes piled within the sink, as the pungent stench of cigarette smoke filled the air.

Once again, the voice on the other side of the door called, "Jess, open this door now! We need to talk!"

"I said go away!" Jess yelled back, as he poured himself a glass of water.

Outside, in the hall, a frustrated young woman sighed. With firm resolve, she stepped back and reached beneath the doormat for the spare key. Jess had been lying on his threadbare mattress reading a book when the girl barged in.

"The next time you decide to go into seclusion, get rid of the spare key first," she scorned, tossing to him the metallic object.

Irritated, Jess sat up and glared at her. "I told you to leave me alone. What part of that don't you understand?"

The young woman just bent down and gazed at him empathetically. For a moment she looked thoughtful until an acrid smell reached her nose.

"Oh, gosh," she exclaimed. "Jess, have you been smoking?"

Jess's jaw tightened as he simply turned away. He was in denial and she knew it. There was something seriously wrong, and he would have had to be a real idiot to think that he could hide it.

"Jess, I've been trying to reach you for two days now. Every time I call, you never pick up, and when I come over, you're never here." She paused, and tried to look into his eyes – those dark eyes of his that seemed to hold so much anger against the world. "Tell me, what's going on with you?"

"Cecilia," he pleaded. "I don't want to talk right now."

"This is about Rory, isn't it?" she asked rather abruptly.

Jess blinked, and then drew in a breath. He didn't reply, but instead dropped his gaze. She knew it; it always went back to Rory. Cecilia sighed, and placed a reassuring hand on his shoulder.

"Jess, you shouldn't–"

"No," he said, pushing her hand away. "She said no."

Cecilia bit her lip as Jess suddenly stood up. For a moment, he paced around the room, as if to gather his thoughts. He finally stopped before her as a look of dejection passed over his rugged face.

"I should have seen it coming. I mean, what was I thinking?"

"Jess," Cecilia began; she gently grabbed his arm.

"It hurt, Cecilia," he confessed. "It hurt a lot." Jess swallowed hard; his gaze was fixed so intently on her that Cecilia dared not move. She felt compelled to speak, but the pain of rejection that clouded his eyes kept her silent.

At long last, he turned away and sighed. "I should have treated her better. Heck, I don't blame her for refusing to go."

And so it was that reality began to hit him. He had lost the one person he truly loved, and this time, there was no chance of getting her back. Cecilia, too, could see that he had come to that revelation. She knew how much Rory meant to Jess, and it troubled her to see him in such a desperate state.

Without warning, she gently embraced him. Although he was caught off guard by the gesture, he didn't resist. It was just what he needed right now. They stayed like that for a moment, until Cecilia pulled away.

"I'm sorry it didn't work out," she said quietly. "But I can't let you throw your life away like this."

Speechless, Jess just turned away and ran his hand through his hair. He hated to admit it, but she was right. It had been two days since the incident with Rory, and he had done nothing but mope around, returning to his old habits of smoking and drinking. He had thrown away all his pride, and he was left with nothing. What else did he have to lose?

"C'mon," Cecilia said, grabbing his hand. "Why don't you go and wash up, and we'll go out to eat? My treat." She smiled.

At first, Jess hesitated; he wasn't exactly feeling sociable at the moment. But, then again, he was starving, and Cecilia's company never failed to cheer him up.

"Alright," he said, smiling meekly. "As long as we're ordering Thai."

Cecilia chuckled. "It's a deal." And with that, she watched him disappear into the bathroom.


	2. Best Man Blues

**Disclaimer: I do not own Gilmore Girls or any of its characters.**

_Hey, you guys. Really appreciate the reviews. Thanks a million! Anyway, enjoy the new chapter! _

**Chapter II: Best Man Blues**

A year and a half later, Jess Mariano would look back on that day as a turning point in his life. It was the day he was acquainted with the pain of sacrifice. And it was the day he learned the meaning of love. His cold and distant exterior never left him, but deep down, he had become more compassionate. But of course, he wouldn't be the first guy to brag about his soft side.

Jess walked out of the bathroom, freshly bathed, as he buttoned up his shirt. The sweet aroma of pancakes and fried eggs led him straight to the kitchen, where his breakfast awaited him. Cecilia stood by the counter, pouring a cup of hot coffee when he entered.

"Good morning," she greeted.

"Hey," he replied, planting a soft kiss on her lips. "Early class today?"

"Yeah," she said, as they took their seat at the table. "Nine o'clock. And then I have a two thirty lecture."

"Until what time?"

"Around four thirty."

"So," he said, with a reluctant glance. "Do you want to me cook dinner or something?"

Cecilia laughed. "And run the risk of food poisoning? I don't think so!"

"Hey, that meatloaf surprise I made last week wasn't that bad."

"Yeah, and the surprise was that it tasted like cat food," she teased.

Jess sent her a playful glare. Though it was all in good humor, he knew wasn't a five-star chef. As he was finishing the last of his pancakes, he was suddenly aware of Cecilia's gaze upon him.

He glanced up. "What?"

Cecilia hesitated and then answered, "I got a phone call from Luke last night."

"Oh yeah?" Jess offhandedly shot back, as he pretended to skim over the newspaper. "How is good old Uncle Luke?"

"Jess," Cecilia contended. "You know his wedding is coming up next week, and he still needs a best man."

Taken aback, Jess sat up and stared at her defiantly. "And what am I supposed to do? Draft myself for the part? I don't think so."

Cecilia frowned. "Now you're just being ungrateful. Don't you think you owe it to him for having to put up with you when you were going through that whole James Dean phase of yours?"

Jess froze; he then sat back in his chair and crossed his arms over his chest. He knew where this was going, and there was no way he was returning to that wretched town of lunatics.

"Besides, I think the timing is perfect, since we have a break next week," she continued.

When it was obvious that Jess wouldn't respond, Cecilia sighed. "C'mon, Jess," she urged. "It'll only be for a while. And don't you think it's about time I get to meet the infamous uncle of the guy that I've been dating for seven months now?"

"Why?" Jess scoffed. "Just so our love life can make it in headline news on the Stars Hollow Gazette?"

Cecilia frowned. "Jess–"

"No," he said resolutely. "I'm not going."

Cecilia pursed her lips, as she sent him a cold glare. Jess's stubbornness was something she came to accept about him. However, when it came to matters like this, his bull-headed self was intolerable. Without a word, she got up from the table and dumped her plate in the sink.

Before she could leave though, Jess quickly grabbed her arm. "Cecilia, don't be like this."

Jess's voice held an indistinct hint of unease that held Cecilia back. At length, she turned to him and smiled apologetically. "I'm sorry. If you really feel uncomfortable going back, I won't–"Jess placed his finger on her lips. "I'll go. But we're not staying there for more than three days."

"You sure?" she asked, raising an eyebrow.

"Positive," he said, staring straight into her eyes.

Cecilia smiled, as she threw her arms around his neck and hugged him. "Thank you. You won't regret it, I promise."

"Let's hope not," Jess muttered to himself, as he held her tightly in his arms.

It was another typical day in Stars Hollow, as the town was busy preparing for the upcoming Firefly Festival. The cool spring morning brought with it the promise of tender warmth, as the sun peeked from behind clouds. Meanwhile, streamers and lanterns were being set up around the gazebo, with Kirk diligently dictating the task force.

"Hey! You don't want to put that there!" Kirk yelled through his bullhorn. "That might be a fire hazard!"

From across the street, Lorelei Gilmore smiled as she observed the town's jack-of-all-trades. Stars Hollow certainly had a place in her heart as far as home was concerned. It was a place where she didn't need to hide behind a white-bred mask of wealth and prominence. Though there were often times of chaos, and though the residents had their share of insanity, Lorelei wholeheartedly felt a sense of belonging in the small town.

"So, how are those wedding plans coming?" Rory asked, as she observed Kirk as well.

"Oh, there coming," she replied with a smile. "Last night, Luke and I made the most important decision of all: which color napkins we were going to use."

"Glad to know your entire marital future depends on a napkin."

"Oh, trust me, it's a big step for us," explained Lorelei with a mock expression. "None of that filibustering crap that we had to go through when we had to pick out the cake, the place, my dress and his tie." She smiled, and draped her arm around her daughter. "And what about you? Has Logan gotten down on one knee yet and agree to be your escort?"

"No, not yet." Rory grinned. "He wants to secure a restraining order for Ms. Patty before he comes here again. Remember what happened last time?"

Lorelei and Rory both laughed at the humorous memory, as they entered Luke's Diner. The placed was packed as usual, and they were forced to take a seat at the counter. As they did so, Luke walked out of the storage room, and upon seeing Lorelei, bent over the counter and gave her a quick kiss.

"Hey," he said with a nod. He paused before asking, "So, are you planning to go to festival?"

"Why?" Lorelei teased. "Are you planning to ask me?"

Luke couldn't help but grin. Lorelei's sarcasm was one of the quirks he had come to love about her. After a while, Luke sighed and bluntly asked, "Do you want to go together or not?"

Lorelei smiled. "Would I ever pass up the chance to spend time with you, my darling Luke?"

"I'll take that as a yes. So, do you girls want the usual?"

"Yes, and make it snappy! I'm starving!" Lorelei exclaimed.

Luke shook his head in disapproval, and turned to leave. Once out he was out of earshot, Lorelei turned to Rory with a deliberate smirk.

"I love that man."

Rory just smiled, and glanced around the diner. The usual morning scent of toast and coffee circulated the building, as the drone of multiple conversations hummed in the background. Suddenly, much to Rory's surprise, she heard the sound of footsteps coming down the stairs from Luke's apartment. Within seconds, Jess appeared behind the counter.

Rory nearly fell out of her chair upon seeing him. "Jess?"

In turn, Jess froze as he met her gaze. Rory Gilmore, a perfect way to start out the morning. He had expected to see her, just not so soon. Jess swallowed hard before nodding his head in acknowledgement.

"Rory." He then turned to Lorelei and with a meek smile greeted, "Hi."

At first, Lorelei blinked in disbelief. "Well," she began. "The circus is back in town. Here for another showstopper, Jess?"

There was always something about this boy that reminded her of fingernails on a chalkboard. It seemed to Lorelei that wherever Jess was, trouble was never too far behind.

Jess just rolled his eyes, as Luke came back with their orders.

Catching the drift of the conversation, Luke quickly replied, "Actually, Jess agreed to be my best man."

Lorelei faltered. "Excuse me? You didn't mention that little detail last night when we were deliberating about napkins."

Before Luke could explain, Cecelia soon appeared behind the counter.

"Good morning, Luke," she greeted with a smile.

"Hey," Luke said. "Did you guys find everything okay last night?"

All the while, a bewildered Lorelei was frantically waving her hands in the air. Did she suddenly turn invisible or what?

"Uh, hello," she called. "It's bad luck for the bride to be out of touch with her own wedding plans."

Luke sighed. "Look, I'm sorry. Yesterday was just so hectic, and then these two showed up–"

With tension closing in, a restless Jess turned to Luke and said, "Cecelia and I are going out for a while. Do you need anything?"

Luke nodded. "Now that you mention it, could you stop by the warehouse and pick up some meat packages? Steve was supposed to drop them off today, but he can't make it."

"Okay," Jess agreed; he briefly glanced at Rory, who turned away grudgingly. "We won't be long."

Once Jess and Cecelia were out the door, Lorelei turned to Luke with firm resolve. "Okay, Luke, what's the story?"

"I told you, he finally agreed to be my best man. You know I've been trying to convince him for weeks to do this. "

Rory frowned at this. Nothing good ever came out of Jess's visits. His last visit – as she recalled – resulted in a sleepless night plagued with heartbreak and regret. Though she had convinced herself to move on, Jess had indeed left her with a sense of bitterness: a wound that forever left a scar in her heart.

Lorelei rolled her eyes. "I didn't think he'd actually agree. What made him change his mind?"

Luke shrugged. "Cecelia probably talked him into it. She's got a way with him; really sweet girl."

"You mean that girl that was just with him?"

"Yeah," Luke said as he cleared his throat. "That was his girlfriend."

At this note, Lorelei almost choked on her coffee, while Rory's expression shifted to subtle astonishment. A girlfriend? The possibility never dawned on Rory before, and yet, she never expected Jess to pine for her after all this time. Either way, the idea seemed to provoke long forgotten emotions. Whether these emotions included jealously or not was another story.

"A girlfriend?" Rory stuttered.

Luke nodded. "They've been going out for seven months now. I think they might actually be living together."

"Well, I'm utterly speechless," stated Lorelei, as she took a bite of her bagel.

Luke knew that Jess was certainly hit a sore spot with the Gilmore girls. Yet, in his nephew's defense, he countered, "Believe me, Jess isn't here to cause trouble."

"Sure," Lorelei exclaimed, sarcasm evident in her voice. "That's what they said about Mussolini."

"I don't know why I bother," Luke muttered as he left to resume with his work.

Lorelei just smiled, then turned to Rory and placed a reassuring hand on her shoulder. "Hey, are you okay?"

"Yeah," Rory replied with a weak smile. "Just didn't expect to see him back here."

"Yes, well, Jess is the master of surprises."

Rory just nodded, as she took a sip of her coffee. Jess and Cecilia. Somehow, the thought of it made her stomach churn. For all she knew, Cecilia could just be another puppet in Jess's act to win over her heart. It surely wouldn't be the first time he's tried. And yet, was she really that shallow to think of Jess in that regard? In spite of herself, Rory pushed the thought aside, determined to not let her emotions get the best of her.


	3. Open Book

**Disclaimer: I do not own Gilmore Girls or any of its characters.**

_So, after a little planning, I've decided that there's going to be a little Jess/Rory romance in here, as well as Jess/Cecilia (needless to say). But as far as the ending goes, can't tell you guys that part. There'd be no point to the story then. Anyway, enjoy the new chapter! _

**Chapter III: Open Book**

Stars Hollow hadn't changed much, Jess thought as he and Cecilia took a drive around the small town. Same shops. Same streets. Same people. Oddly enough, he felt almost at home when he arrived in town last night; almost as if he found a part of him that he had lost a long time ago.

"This place looks like something out of a Hallmark card," Cecilia mused, looking at the decorations for the festival.

Jess scoffed, "I wouldn't count on it."

Cecilia then turned to Jess, her hazel eyes fixed thoughtfully on him.

"So that was Rory," she said quietly.

She had seen the way he looked at her. She saw the way she looked at him. There was an unfinished business between them, and Cecilia knew she had no place in it. Nevertheless, she couldn't help but feel a pang of worry course through her veins.

Jess kept his eyes on the road, seemingly unfazed by her comment. He was determined to keep Rory off his mind, for both his and Cecilia's sake. He remained silent, and Cecilia decided to drop the subject. She'd known him long enough to know how far she could push the envelope.

In an attempt to break the awkward tension, Cecilia asked, "So, how about that Firefly Festival tonight? Are we going?"

As the car approached a red light, Jess met Cecilia's gaze. "Why? Do you want to go?"

"I don't know." She shrugged. "It might be fun."

Jess let his eyes wander over the delicate contours of her face, and he let his heart swell in the endearing affection he held for the girl before him. In spite of himself, he reached out and held her hand.

"Alright," he gently said. "We'll go."

Cecilia smiled. "Alright." And with that, she bent over a placed a lingering kiss on his lips.

Later that day, while Cecilia went out to run some errands, Jess was up in Luke's apartment typing away on his laptop. Nearly a year ago, he had started writing his own novel and he was determined to finish it. Although the story was fictional, it was intended to reflect him and his experiences.

Hitting a snag in his train of thought, Jess sat back in his chair and sighed. For several minutes, he stared at the computer screen, hoping that the words he needed to continue the narrative would magically reveal themselves to him. No good, Jess thought as he stood up and stretched. Moving over to the window, he leaned against the wall and gazed at the town below. Kids were running along the street and the trees were swaying in the wind. And from the looks of it, Kirk and Taylor had gotten into another petty argument.

Soon enough, Jess reached into his pocket and pulled out a small velvet box. He stared at it seemingly deep in thought when, suddenly, Luke came in.

"Hey," he said as he headed for the fridge. "What are you doing?"

By then, Jess had quickly slipped the box back into his pocket. "Writing," he replied, returning to his laptop.

Luke began rummaging through the items in the fridge, looking for a fresh jar of pickles. The sound of scraping cans and clanging jars was soon enough noise to force Jess to relinquish his writing attempt altogether.

At length, Luke asked, "Where's Cecilia?"

Jess stared pointedly at Luke. "Out."

"You know, she really is a great girl," Luke commented as he continued to sort through the fridge.

"That's why I'm planning to marry her," Jess muttered under his breath.

Apparently, Luke didn't hear Jess's statement as he stood up and exclaimed, "Aha! I knew I had it lying around somewhere."

Jess just remained silent as he watched Luke head for the door. Before he left, however, he turned to his nephew and asked, "Oh, did you say something?"

Jess shook his head.

"Okay," Luke said, eyeing him suspiciously. "Well, anyway, if you could come down later and help me close up, that'd be great. I'm taking Lorelei to the festival tonight."

"Okay," Jess replied, as he watched Luke exit the room.

Once his uncle was gone, Jess pulled the box out again and opened it. Often, the thought behind the ring – the thought of her – was enough to revamp his urge to write. And at that moment, it was just the inspiration he needed to break him free from his writer's block. After running his finger over the silver band, Jess closed the box and continued on with his novel.

Meanwhile, Cecilia had been roaming around town, touring and window-shopping. Her curiosity, however, led her to reflect on the insane reputation Jess had conjured up for Stars Hollow. She knew almost everyone before arriving in town, and being able to meet them in person made it all the more exciting for her.

As she was passing by Andrew's book store, Cecilia suddenly spotted a book she had been dying to get a hold of for months. Without a moment's hesitation, she entered the shop and grabbed the book from the shelf. She took a minute to leaf through the book and skim over the pages before making her way to the cash register. As she was turning a corner however, Cecilia accidentally bumped into someone, causing a stack of books to plummet onto the floor.

"Oh, I'm sorry," Cecilia quickly apologized. "Here let me help you with that."

"No, that's okay," the person replied.

Recognizing the person's voice, Cecilia froze and glanced up only to see Rory with a meek smile across her face. Cecilia had no choice but to smile back, though uneasily, and continue picking up the books.

"Here you go," she said, handing the stack of novels to Rory.

"Uh, thanks."

The two girls both stood there for a moment, unsure of their next move. With the silence growing into a suffocating tension, Cecilia decided to break the awkward.

"So," she began. "I saw you at Luke's Diner this morning. Rory, right? Lorelei's daughter?"

"Yeah," Rory replied with a slight nod. "And you must be Cecilia. Luke mentioned you earlier."

"Oh, did he?"

"Yeah."

Cecilia bit her lip and Rory rubbed her arm, as they both fell into another lull.

At length, Cecilia sighed with exasperation and said, "Look, I'm just going to say what we're both not saying and let the chips fall." She paused and looked at a bewildered Rory before continuing. "I know about you and Jess. I know that you guys used to date. I know the whole story."

Taken aback by Cecilia's candor, Rory was at loss for words.

Cecilia gave an apologetic smile. "I just thought you should know."

She then turned around and headed for the cash register.

As she was leaving, however, Rory called to her and asked, "Are you going to the festival tonight?"

"Yeah," Cecilia replied.

With a small smile, Rory said, "I'll see you there then."

Cecilia blinked for a moment before returning the gesture. "Okay, see you there."


End file.
